Fluorine containing heterocyclic compounds: synthesis of 6-substituted-2-substituted-aryl-1,2,4-triazolo[5,1-b] 1,3,5-thiadiazin-7-one derivatives

A group of heterocylic compounds of condensed triazole-thiadiazinone deriva tives containing fluorine (ma-h) were obtained in good yields by the reacti ons of the corresponding 3-aryl-5-mercapto-1,2,4-triazole (IIa-d) with N-su bstituted-N-chloromethyl carbamoyl chloride (I) in the presence of potassiu m carbonate in N,N-dimethylformamide at room temperature. Cyclization of 3- (2,3,5-trifluoro-4-methoxyl)phenyl-5-mercapto-1,2,4-triazole (IIe) with I w as difficult due to an intermolecular hydrogen bond of IIe. The structures of the compounds synthesized were confirmed by LR, MS, H-1 NMR and elementa l analyses. Fungicidal and insecticidal activities of these compounds were also studied. (C) 2000 Elsevier Science S.A. All rights reserved.